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    Lec 17 - Reaction Analogies and Carbonyl Reactivity

    "Lec 17 - Reaction Analogies and Carbonyl Reactivity" Freshman Organic Chemistry (CHEM 125) Continuing the examination of molecular orbital theory as a predictor of chemical reactivity, this lecture focuses on the close analogy among seemingly disparate organic chemistry reactions: acid-base, SN2 substitution, and E2 elimination. All these reactions involve breaking existing bonds where LUMOs have antibonding nodes while new bonds are being formed. The three-stage oxidation of ammonia by elemental chlorine is analyzed in the same terms. The analysis is extended to the reactivity of the carbonyl group and predicts the trajectory for attack by a high HOMO. This predicted trajectory was validated experimentally by Bürgi and Dunitz, who compared numerous crystal structures determined by X-ray diffraction. 00:00 - Chapter 1. Similarities Among Acid-Base, SN2 Substitution, and E2 Elimination Reactions 15:23 - Chapter 2. The Oxidation of Ammonia by Chlorine in Molecular Orbital Terms 26:05 - Chapter 3. Reactivity of the Carbonyl Group 36:11 - Chapter 4. Dunitz and Burgi's Experimental Results on Carbonyl Attack Trajectory Complete course materials are available at the Open Yale Courses website: http://open.yale.edu/courses This course was recorded in Fall 2008.

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    Lec 1 - How Do You Know?

    Lec 2 - Force Laws, Lewis Structures and Resonance

    Lec 3 - Double Minima, Earnshaw's Theorem and Plum-Puddings

    Lec 4 - Coping with Smallness and Scanning Probe Microscopy

    Lec 5 - X-Ray Diffraction

    Lec 6 - Seeing Bonds by Electron Difference Density

    Lec 7 - Quantum Mechanical Kinetic Energy

    Lec 8 - One-Dimensional Wave Functions

    Lec 9 - Chladni Figures and One-Electron Atoms

    Lec 10 - Reality and the Orbital Approximation

    Lec 11 - Orbital Correction and Plum-Pudding Molecules

    Lec 12 - Overlap and Atom-Pair Bonds

    Lec 13 - Overlap and Energy-Match

    Lec 14 - Checking Hybridization Theory with XH_3

    Lec 15 - Chemical Reactivity: SOMO, HOMO, and LUMO

    Lec 16 - Recognizing Functional Groups

    Lec 18 - Amide, Carboxylic Acid and Alkyl Lithium

    Lec 19 - Oxygen and the Chemical Revolution (Beginning to 1789)

    Lec 20 - Rise of the Atomic Theory (1790-1805)

    Lec 21 - Berzelius to Liebig and Wöhler (1805-1832)

    Lec 22 - Radical and Type Theories (1832-1850)

    Lec 23 - Valence Theory and Constitutional Structure (1858)

    Lec 24 - Determining Chemical Structure by Isomer Counting (1869)

    Lec 25 - Models in 3D Space (1869-1877); Optical Isomers

    Lec 26 - Van't Hoff's Tetrahedral Carbon and Chirality

    Lec 27 - Communicating Molecular Structure in Diagrams and Words

    Lec 28 - Stereochemical Nomenclature; Racemization and Resolution

    Lec 29 - Preparing Single Enantiomers and the Mechanism of Optical Rotation

    Lec 30 - Esomeprazole as an Example of Drug Testing and Usage

    Lec 31 - Preparing Single Enantiomers and Conformational Energy

    Lec 32 - Stereotopicity and Baeyer Strain Theory

    Lec 33 - Conformational Energy and Molecular Mechanics

    Lec 34 - Sharpless Oxidation Catalysts and the Conformation of Cycloalkanes

    Lec 35 - Understanding Molecular Structure and Energy through Standard Bonds

    Lec 36 - Bond Energies, the Boltzmann Factor and Entropy

    Lec Last - Potential Energy Surfaces, Transition State Theory and Reaction Mechanism